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The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray).

ABSTRACT: In the title compound, C(24)H(29)ClO(8)·2.5H(2)O, which contains two organic mol-ecules (A and B) and five heavily disordered water mol-ecules in the asymmetric unit, the ?-lactone ring and the cyclo-hexenone ring are both trans-fused to the central cyclo-decene ring. The cyclehexenone ring features an ?,?-unsaturated ketone with torsion angles between the conjugated carbonyl and alkene bonds of 0.6?(3) and 7.4?(4)° for mol-ecules A and B, respectively. The ptilosarcenone torsion angles between conjugated alkene bonds are 56.2?(5) and 55.4?(6)° for A and B, respectively. In the crystal, the components are linked by O-H?O hydrogen bonds. The absolute configuration of ptilosarcenone was determined unambiguously and exhibits similar absolute stereochemistry to that found in the crystal structures of other octocoralline briaranes.

SUBMITTER: Nurco DJ

PROVIDER: S-EPMC3050379 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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The absolute structure of ptilosarcenone 2.5-hydrate, a diterpenoid briarane from the orange sea pen Ptilosarcus gurneyi (Gray).

Nurco Daniel J DJ Conklin Douglas E DE Shapiro Nathan S NS Tran Elaine E

Acta crystallographica. Section E, Structure reports online 20101218 Pt 1

In the title compound, C(24)H(29)ClO(8)·2.5H(2)O, which contains two organic mol-ecules (A and B) and five heavily disordered water mol-ecules in the asymmetric unit, the γ-lactone ring and the cyclo-hexenone ring are both trans-fused to the central cyclo-decene ring. The cyclehexenone ring features an α,β-unsaturated ketone with torsion angles between the conjugated carbonyl and alkene bonds of 0.6 (3) and 7.4 (4)° for mol-ecules A and B, respectively. The ptilosarcenone torsion angles between ...[more]

PMID: 21522687

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